European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 16

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Impact Factor: 3.154

ISI Journal Citation Reports © Ranking: 2013: 14/58 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

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  1. 1 - 68
  1. Short Communications

    1. Asymmetric Alkynylation

      Enabling Asymmetric Alkynylation of Azaaryl Aldehydes with Soai Autocatalyst

      Matías Funes-Maldonado, Bora Sieng and Mohamed Amedjkouh

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500507

      Thumbnail image of graphical abstract

      Amplification and propagation of asymmetry: Soai compound, generated by autocatalytic asymmetric amplification in up to 99.5 % ee, acts as a highly efficient catalyst for the ensuing asymmetric alkynylation of azaaryl aldehydes to produce alkynols with up to 86 % ee.

  2. Full Papers

    1. Diastereoselective Addition

      Diastereoselective Construction of 3-Aminooxindoles with Adjacent Stereocenters: Stereocontrolled Addition of γ-Substituted Allylindiums to Isatin Ketimines

      Nayyar Ahmad Aslam, Srinivasarao Arulananda Babu, Soniya Rani, Shivam Mahajan, Jagmohan Solanki, Makoto Yasuda and Akio Baba

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500340

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      A synthetic protocol for the diastereoselective indium-mediated Barbier-type C–C bond formation has been developed. The addition of γ-substituted allylic reagents to the C=N bond of isatin ketimines was employed for the synthesis of several new 3-aminooxindoles that have two contiguous stereocenters.

    2. Mannich Reactions

      Mechanism Switch in Mannich-Type Reactions: ELF and NCI Topological Analyses of the Reaction between Nitrones and Lithium Enolates

      David Roca-López, Victor Polo, Tomás Tejero and Pedro Merino

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500447

      Thumbnail image of graphical abstract

      Depending on the type of enolate the reaction mechanism changes from one-step to stepwise.

  3. Short Communications

    1. Cationic Cyclization

      Synthesis of Perfluoroalkyl-Substituted Vinylcyclopropanes by Way of Enhanced Neighboring Group Participation

      Christopher B. Kelly, Michael A. Mercadante, Emma R. Carnaghan, Matthew J. Doherty, Diana C. Fager, John J. Hauck, Allyson E. MacInnis, Leon J. Tilley and Nicholas E. Leadbeater

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500565

      Thumbnail image of graphical abstract

      A diverse array of fluoroalkyl-substituted vinylcyclopropanes are prepared in a simple, high-yielding, two-step, one-pot protocol by means of cationic ring-closure.

    2. Fluorination

      Synthesis of 5-Fluorotriazoles by Silver-Mediated Fluorination of 5-Iodotriazoles

      Damin Wang, Wenjing Sun and Taiwei Chu

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500338

      Thumbnail image of graphical abstract

      A new strategy for the direct fluorination of 5-iodotriazoles with AgF and N1,N1,N2,N2-tetramethylethane-1,2-diamine (TMEDA) is described. Substrates with aliphatic or aromatic groups at the N1 position or 4-position can be converted to the corresponding fluorinated products in good to excellent yields. Preliminary mechanism studies were also performed.

  4. Full Papers

    1. Tandem Cyclization

      A Cascade Approach to Naphthalene Derivatives from o-Alkynylbenzaldehydes and Enolizable Ketones via in-situ-Formed Acetals

      Seetharaman Manojveer and Rengarajan Balamurugan

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500497

      Thumbnail image of graphical abstract

      In situ acetal formation assists the intermolecular cyclization of o-alkynyl aryl aldehydes with enolizable ketones to give diverse naphthyl ketone derivatives under metal-free catalytic conditions.

  5. Short Communications

    1. Asymmetric Amplification

      Asymmetric Amplification Coupling Enantioselective Autocatalysis and Asymmetric Induction for Alkylation of Azaaryl Aldehydes

      Carlo Romagnoli, Bora Sieng and Mohamed Amedjkouh

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500508

      Thumbnail image of graphical abstract

      Amplification and propagation of asymmetry: Soai autocatalyst is amplified in situ from 11 % to > 98 % ee and concomitantly catalyzes the addition of Zn(iPr)2 to azaaryl aldehydes to provide alkanols with up to 99 % ee. Also, exceptional amplifications of ee in one cycle are observed for both compounds.

  6. Full Papers

    1. Thioethers

      One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme

      Mohammad Gholinejad

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500256

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      A copper-catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.

    2. Insect Pheromone Research

      Pheromone Bouquet of the Dried Bean Beetle, Acanthoscelides obtectus (Col.: Chrysomelidae), Now Complete

      József Vuts, Wittko Francke, Kenji Mori, Paulo H. G. Zarbin, Antony M. Hooper, Jocelyn G. Millar, John A. Pickett, Miklós Tóth, Keith Chamberlain, John C. Caulfield, Christine M. Woodcock, Armin G. Tröger, Éva Bálintné Csonka and Michael A. Birkett

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500196

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      The male-produced sex pheromone of the dried bean beetle Acanthoscelides obtectus consists of ethyl (E,R)-2,4,5-tetradecatrienoate, methyl (2E,4Z)-decadienoate, methyl (2E,4Z,7Z)-2,4,7-decatrienoate, octadecanal and (3Z,6E)- as well as (3E,6E)-α-farnesene. A complete blend of synthetic compounds in natural proportions was as attractive as the natural signal.

    3. Domino Reactions

      Intra-Intermolecular Palladium-Catalyzed Domino Reactions of Glycine Allylamides for the Synthesis of Diversely Functionalized Piperazinones

      Gianluigi Broggini, Egle M. Beccalli, Tea Borelli, Filippo Brusa, Silvia Gazzola and Alberto Mazza

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500386

      Thumbnail image of graphical abstract

      Inter-intramolecular domino palladium-catalyzed reactions of N-tosylglycine allylamides were used to access piperazinones with functional groups that can undergo further transformations. Aminochlorination and aminoacetoxylation processes were achieved by using CuCl2 and PhI(OAc)2 as oxidizing agents to give 5-chloromethyl- and 5-acetoxymethyl-substituted piperazinones, respectively.

  7. Short Communications

    1. Anion Templation

      Sulfate Anion as a pH-Switchable Template: Three-State Switchable Systems Based on Diamidocarbazoles

      Krzysztof M. Bąk and Michał J. Chmielewski

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500546

      Thumbnail image of graphical abstract

      The sulfate anion SO42– – one of the most versatile anionic templates – can be reversibly “switched off” in aprotic solvents by protonation to the very weakly binding HSO4 anion. This sharp ON/OFF behaviour opens new opportunities for switching and manipulation of supramolecular systems, as demonstrated here by the construction of two new acid/base switchable three-state systems.

  8. Full Papers

    1. Porphyrinoids

      Synthesis of Functionalized BODIPYs, BODIPY-Corrole, and BODIPY-Porphyrin Arrays with 1,2,3-Triazole Linkers Using the 4-Azido(tetrafluorophenyl)-BODIPY Building Block

      Hartwig R. A. Golf, Anna M. Oltmanns, Duc H. Trieu, Hans-Ulrich Reissig and Arno Wiehe

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500413

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      The synthesis of meso-functionalized BODIPYs using the copper(I)-catalyzed cycloaddition of terminal alkynes with an azido-substituted BODIPY is presented. The scope of this reaction was extended to the synthesis of OH- and SF5-substituted BODIPY-CuIII-corrole and BODIPY-ZnII-porphyrin arrays, demonstrating a versatile approach towards multichromophoric systems.

  9. Short Communications

    1. Statin Synthesis

      A Practical Synthesis of Rosuvastatin and Other Statin Intermediates

      Stefano Tartaggia, Clark Ferrari, Marta Pontini and Ottorino De Lucchi

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500356

      Thumbnail image of graphical abstract

      A new synthetic approach to statins has been developed. The efficient aldol condensation of heterocyclic aldehydes comprising the core structure of rosuvastatin and pitavastatin with a derivative of methyl 3-hydroxy-5-oxohexanoate affords products with the desired E geometry in high yield.

  10. Microreviews

    1. The Nugent Reagent

      The Nugent Reagent: A Formidable Tool in Contemporary Radical and Organometallic Chemistry

      Antonio Rosales, Ignacio Rodríguez-García, Juan Muñoz-Bascón, Esther Roldan-Molina, Natalia M. Padial, Laura Pozo Morales, Marta García-Ocaña and J. Enrique Oltra

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500292

      Thumbnail image of graphical abstract

      The different reactions promoted and/or catalysed by the Nugent reagent, a contemporary single-electron transfer agent, are reported. The combination of radical intermediates and transition-metal catalysis is an excellent tool for the development of new and efficient synthetic procedures.

  11. Full Papers

    1. Multicomponent Reactions

      Iron-Catalysed Oxidative Ugi-Type Multicomponent Reaction Using (Arylmethyl)amines as Imine Precursors

      Shashikant U. Dighe, Shivalinga Kolle and Sanjay Batra

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500464

      Thumbnail image of graphical abstract

      The oxidative three-component Ugi reaction catalysed by Fe(NO3)3·9H2O using (arylmethyl)amine as the imine source under aerobic conditions is described.

  12. Microreviews

    1. β-Fluorinated Amines

      Advancements in Aminofluorination of ­Alkenes and Alkynes: Convenient Access to β-Fluoroamines

      Pinhong Chen and Guosheng Liu

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500231

      Thumbnail image of graphical abstract

      Direct aminofluorination of alkenes enables the convenient synthesis of β-fluorinated amine compounds, which are important and valuable building blocks in medicinal chemistry. This review covers recently developed methods for aminofluorination of alkenes, mainly focusing on transition-metal-catalyzed pathways.

  13. Full Papers

    1. Azonia Aromatic Cations

      Azonia Aromatic Cations by Ring-Closing Metathesis: Synthesis of Azaquinolizinium Cations

      Alberto Abengózar, Beatriz Abarca, Ana M. Cuadro, David Sucunza, Julio Álvarez-Builla and Juan J. Vaquero

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500404

      Thumbnail image of graphical abstract

      A new approach for the synthesis of the 1-azaquinolizinium (pyrimido[1,2-a]pyrimidin-5-ium) heterocycle and some simple derivatives is described. This strategy, based on an unprecedented ring-closing metathesis (RCM) reaction to construct the pyrimidinium ring, was also applied to the first reported synthesis for the benzo-1-azaquinolizinium (pyrimido[2,1-a]isoquinolinium) cation.

    2. Natural Product Synthesis

      Synthesis and Biological Evaluation of Dichlorinated Chondramide Derivatives

      Dominic Becker and Uli Kazmaier

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500369

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      Investigation of the methyl-substitution pattern in the polyketide fragment of new ethyl-substituted dichlorinated chondramides.

  14. Short Communications

    1. Photocatalysis

      Synthesis of β-Trifluoromethylated Ket­ones from Propargylic Alcohols by Visible Light Photoredox Catalysis

      Sehyun Park, Jung Min Joo and Eun Jin Cho

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500031

      Thumbnail image of graphical abstract

      β-Trifluoromethyl ketones are synthesized from readily available propargylic alcohols by visible light photocatalysis. Trifluoromethylation followed by double-bond migration/keto-enol tautomerization provides β-trifluoromethyl ketones as the final product.

  15. Full Papers

    1. Copper-Catalyzed Amination

      N-(1-Oxy-2-picolyl)oxalamic Acid as an Efficient Ligand for Copper-Catalyzed Amination of Aryl Iodides at Room Temperature

      Yongbin Wang, Jing Ling, Yu Zhang, Ao Zhang and Qizheng Yao

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500279

      Thumbnail image of graphical abstract

      N-(1-Oxy-2-picolyl)oxalamic acid was identified as an efficient ligand for promoting Cu-catalyzed amination of aryl halides with aliphatic amines and ammonia at room temperature.

    2. Medium-Ring Heterocycles

      Gold- and Silver-Catalyzed 7-endo-dig Cyclizations for the Synthesis of Oxazepines

      Anatoly A. Peshkov, Anton A. Nechaev, Olga P. Pereshivko, Jan L. Goeman, Johan Van der Eycken, Vsevolod A. Peshkov and Erik V. Van der Eycken

      Article first published online: 22 MAY 2015 | DOI: 10.1002/ejoc.201500357

      Thumbnail image of graphical abstract

      A comprehensive study on gold- and silver-catalyzed cycloisomerizations of hydroxypropargylamides into oxazepines is described.

    3. Cross-Coupling

      First Application of Heterogeneous Cobalt Catalysis in Csp2–N Cross-Coupling of Activated Chloroarenes under Ligand-Free Conditions

      Nirmalya Mukherjee, Tanmay Chatterjee and Brindaban C. Ranu

      Article first published online: 19 MAY 2015 | DOI: 10.1002/ejoc.201500418

      Thumbnail image of graphical abstract

      A heterogeneous CoII/Al2O3 catalyst efficiently catalyses the N-arylation of N-heterocycles and open- or closed-chain secondary amines by activated chloroarenes and chloroheteroarenes under ligand-free conditions in water to give a series of functionalized tertiary amines.

    4. Heteroatom Effects

      A Joint Experimental–Computational Comparative Study of the Pd0-Catalysed Reactions of Aryl Iodides and Aldehydes with N, O, and S Tethers

      Daniel Solé, Francesco Mariani and Israel Fernández

      Article first published online: 19 MAY 2015 | DOI: 10.1002/ejoc.201500393

      Thumbnail image of graphical abstract

      The influence of the heteroatom on the outcome of intramolecular palladium-catalysed reactions of aryl iodides and aldehydes is explored by means of experimental and computational tools.

    5. Organometallic Chemistry

      Double C–H Functionalization to Construct Polycyclic Heteroarenes Catalyzed by an Ionic Salt of a Pd Complex with an N-Heterocyclic Carbene Ligand

      Sanjay Kumar Ghosh, Bing-Chiuan Kuo, Hsiang-Yu Chen, Jia-Ying Li, Shuang-De Liu and Hon Man Lee

      Article first published online: 19 MAY 2015 | DOI: 10.1002/ejoc.201500417

      Thumbnail image of graphical abstract

      The complex cis-[Pd(L)(PPh3)(H2O)2](SO3CF3)2, in which L is an amido-functionalized N-heterocyclic carbene (NHC) ligand, has been prepared. This complex was effective in catalyzing the double C–H functionalization of various nitrogen- and sulfur-containing heteroarenes to form fused polycyclic heteroaromatic compounds with alkynes in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide.

  16. Microreviews

    1. Niobium Complex Chemistry

      Niobium Complexes in Organic Transformations: From Stoichiometric Reactions to Catalytic [2+2+2] Cycloaddition Reactions

      Yasushi Satoh and Yasushi Obora

      Article first published online: 19 MAY 2015 | DOI: 10.1002/ejoc.201500358

      Thumbnail image of graphical abstract

      Niobium can exist in a number of different oxidation states (from +5 to –3), and it is anticipated that Nb complexes should possess unique reactivity in organic transformations. Previously, low-valent niobium complexes were used as reagents in organic reactions. In recent decades they have been used as catalysts in various [2+2+2] cycloadditions.

  17. Full Papers

    1. Total Synthesis

      A Concise and Efficient Total Synthesis of Militarinone D

      Uttam Dash, Sandip Sengupta and Taebo Sim

      Article first published online: 15 MAY 2015 | DOI: 10.1002/ejoc.201500380

      Thumbnail image of graphical abstract

      A highly efficient (15 % overall yield) and convergent (longest linear sequence of 14 steps) synthesis of militarinone D from a known intermediate has been accomplished.

    2. Concise Synthesis of All Stereoisomers of Dendroamide A by Fluorous Mixture Synthesis Based on Fluorous-Fmoc Protection of Amino Acids

      Hiroaki Takahashi, Natsuki Endo, Hitomi Takanose, Yuya Sugiyama, Fumitaka Eguchi, Kazuma Oguri, Hiromi Hamamoto, Takayuki Shioiri and Masato Matsugi

      Article first published online: 15 MAY 2015 | DOI: 10.1002/ejoc.201500394

      Thumbnail image of graphical abstract

      All eight stereoisomers of dendroamide A have been concisely synthesized by fluorous mixture synthesis based on an encoding strategy of amino acid stereocenters by using fluorous-Fmoc reagents.

    3. Resorcylic Acid Lactones

      A Carbohydrate Approach for the First Total Synthesis of Cochliomycin C: Stereoselective Total Synthesis of Paecilomycin E, Paecilomycin F and 6′-epi-Cochliomycin C

      Bakkolla Mahankali and Pabbaraja Srihari

      Article first published online: 15 MAY 2015 | DOI: 10.1002/ejoc.201500395

      Thumbnail image of graphical abstract

      The first total synthesis of the chlorinated resorcylic acid lactone cochliomycin C is achieved starting from the readily available sugar D-lyxose. The strategy has also lead to the total synthesis of paecilomycin E, paecilomycin F and 6′-epi-cochliomycin C. The key reactions include Ohira–Bestmann alkynylation, ring closing metathesis and regioselective methylation under Mitsunobu conditions.

    4. Pyridine Functionalization

      Functionalization of a Pyridine Framework through Intramolecular Reissert–Henze Reaction of N-(Carbamoyloxy)pyr­idinium Salts and Unexpected Insertion of Ethereal Solvents

      Haruyasu Asahara, Asuka Kataoka, Shotaro Hirao and Nagatoshi Nishiwaki

      Article first published online: 15 MAY 2015 | DOI: 10.1002/ejoc.201500443

      Thumbnail image of graphical abstract

      A new strategy that gives 2-pyridyl carbamates upon treatment of N-(carbamoyloxy)pyridinium salts with silver oxide is reported. Additionally, a new rearrangement of the acyloxy group, combined with insertion of an ethereal solvent to give pyridine derivatives with a coordinating tether, is reported.

    5. Total Synthesis of Isodesmosine

      Total Synthesis of Isodesmosine by Stepwise, Regioselective Negishi and Sonogashira Cross-Coupling Reactions

      Yohei Koseki, Takanori Sugimura, Keita Ogawa, Rina Suzuki, Haruka Yamada, Noriyuki Suzuki, Yoshiro Masuyama, Yong Y. Lin and Toyonobu Usuki

      Article first published online: 15 MAY 2015 | DOI: 10.1002/ejoc.201500449

      Thumbnail image of graphical abstract

      The total synthesis of isodesmosine, a crosslinking amino acid of elastin and an attractive biomarker of COPD, has been achieved by stepwise and regioselective Negishi and Sonogashira cross-coupling reactions.

    6. Gold(I) Catalysis

      Annulated N-Heterocycles by Tandem Gold(I)-Catalyzed [3,3]-Rearrangement/Nazarov Reaction of Propargylic Ester Derivatives: an Experimental and Computational Study

      Martina Petrović, Dina Scarpi, Béla Fiser, Enrique Gómez-Bengoa and Ernesto G. Occhiato

      Article first published online: 15 MAY 2015 | DOI: 10.1002/ejoc.201500462

      Thumbnail image of graphical abstract

      The gold(I)-catalyzed tandem rearrangement/Nazarov reaction of suitable propargylic ester derivatives is a useful strategy for the synthesis of cyclopenta-fused N-heterocyclic structures present in many natural compounds. The process has been studied both experimentally and computationally in details to understand both regio- and torquoselectivity, and to assess its scope and limitations.

  18. Short Communications

    1. Multicomponent Reactions

      Vicinal Functionalization of N-Alkoxyen­amines: Tandem Umpolung Phenylation–Nucleophilic Addition Reaction Sequence

      Shohei Sato, Norihiko Takeda, Tetsuya Miyoshi, Masafumi Ueda and Okiko Miyata

      Article first published online: 15 MAY 2015 | DOI: 10.1002/ejoc.201500308

      Thumbnail image of graphical abstract

      An efficient and four-component reaction was developed. The double nucleophilic reaction of N-alkoxyenamines, derived in situ from aldehyde and isoxazolidine, afforded functionalized amines.

  19. Full Papers

    1. Helimeric Porphyrinoids

      Indaphyrins and Indachlorins: Optical and Chiroptical Properties of a Family of Helimeric­ Porphyrinoids

      Daniel C. G. Götz, Andreas C. Gehrold, Sarina J. Dorazio, Pedro Daddario, Lalith Samankumara, Gerhard Bringmann, Christian Brückner and Torsten Bruhn

      Article first published online: 11 MAY 2015 | DOI: 10.1002/ejoc.201500511

      Thumbnail image of graphical abstract

      Indaphyrins and indachlorins possess persistent helimeric conformations giving rise to separable enantiomeric pairs. The origins of their optical and chiroptical properties were elucidated.

  20. Short Communications

    1. Peptide Catalysis

      Peptide-Catalyzed Desymmetrization of an Achiral Ferrocenyl Compound To Induce Planar Chirality

      Kengo Akagawa, Midori Akiyama and Kazuaki Kudo

      Article first published online: 11 MAY 2015 | DOI: 10.1002/ejoc.201500428

      Thumbnail image of graphical abstract

      Planar chirality was induced on an achiral ferrocenyl compound by peptide-catalyzed desymmetrization. Although such an asymmetric reaction could not be realized with a low-molecular-weight catalyst, a resin-supported peptide with a turn structure afforded products in a highly enantioselective manner.

  21. Full Papers

    1. Glycosylation

      AuCl3– and AuCl3–Phenylacetylene-Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates

      Rashmi Roy, Ashok Kumar Palanivel, Asadulla Mallick and Yashwant D. Vankar

      Article first published online: 8 MAY 2015 | DOI: 10.1002/ejoc.201500137

      Thumbnail image of graphical abstract

      We have reported a convenient room temperature protocol that employs AuCl3 and phenylacetylene as a catalyst system to carry out the glycosylation of glycosyl trichloroacetimidates. The effectiveness of this relay catalyst system was also compared with that of using AuCl3 alone to catalyze the glycosylations.

    2. β-Lactam Synthesis

      Diversity-Oriented Synthesis of β-Lactams and γ-Lactams by Post-Ugi Nucleophilic Cyclization: Lewis Acids as Regioselective Switch

      Zhenghua Li, Upendra Kumar Sharma, Zhen Liu, Nandini Sharma, Jeremy N. Harvey and Erik V. Van der Eycken

      Article first published online: 8 MAY 2015 | DOI: 10.1002/ejoc.201500270

      Thumbnail image of graphical abstract

      A regioselective approach for the synthesis of heterocyclic fused α-methylene β-lactams and α,β-unsaturated γ-lactams by employing a Ugi reaction followed by InIII- or AlIII-catalyzed intramolecular nucleophilic addition is reported.

  22. Short Communications

    1. Ru-Chiral Pincer Complexes

      Synthesis of a P-Stereogenic PNPtBu,Ph ­Ruthenium Pincer Complex and Its Application in Asymmetric Reduction of ­Ketones

      Ismael Arenas, Omar Boutureira, M. Isabel Matheu, Yolanda Díaz and Sergio Castillón

      Article first published online: 8 MAY 2015 | DOI: 10.1002/ejoc.201500389

      Thumbnail image of graphical abstract

      P-stereogenic PNPtBu,Ph Ru complex was for the first time synthesized and characterized and has proven to be an efficient catalyst for the asymmetric reduction of a wide range of ketones

    2. Nitrogen Heterocycles

      A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]­pyridazin-4(1H)-ones

      Cun Tan, Haoyue Xiang, Qian He and Chunhao Yang

      Article first published online: 8 MAY 2015 | DOI: 10.1002/ejoc.201500422

      Thumbnail image of graphical abstract

      A copper(II)-catalyzed tandem synthesis of 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones from N-aminopyrroles was developed, and the corresponding products could be converted directly into diverse pyrrolo[1,2-b]pyridazine for drug discovery and materials science.

  23. Full Papers

    1. Photoswitches

      Dihydroazulene/Vinylheptafulvene Photo­switch: Ultrafast Back Reaction Induced by Dihydronaphthalene Annulation

      Søren Lindbæk Broman, Oleg Kushnir, Martin Rosenberg, Anders Kadziola, Joerg Daub and Mogens Brøndsted Nielsen

      Article first published online: 7 MAY 2015 | DOI: 10.1002/ejoc.201500320

      Thumbnail image of graphical abstract

      The switching rate for the DHA/VHF photoswitch has been changed from minutes to milliseconds by structural modification; locking the VHF in a reactive conformation, the rate of the back reaction (VHF [RIGHTWARDS ARROW] DHA) was increased by a factor of up to 950000. Also, sulfur anchoring groups were attached, possibly allowing the future exploitation of this fast photoswitch in molecular electronics.

    2. Asymmetric Synthesis

      Asymmetric Enynylation of N-Sulfonyl ­Aldimines Catalyzed by Zn-BINOL Complexes

      Zhen-Yan Yang, Tian-Lin Liu, Yan Zheng, Shen Li and Jun-An Ma

      Article first published online: 7 MAY 2015 | DOI: 10.1002/ejoc.201500400

      Thumbnail image of graphical abstract

      An efficient catalytic enantioselective enynylation of N-sulfonyl aldimines is developed. In the presence of Zn-BINOL complexes, a series of enynylated carbinamines was obtained in up to 96 % yield and 95 % ee.

    3. C–H Functionalization

      Palladium-Catalyzed C2-Acylation of Indoles with α-Diketones Assisted by the Removable N-(2-Pyrimidyl) Group

      Chunpu Li, Wei Zhu, Shuangjie Shu, Xiaoming Wu and Hong Liu

      Article first published online: 6 MAY 2015 | DOI: 10.1002/ejoc.201500304

      Thumbnail image of graphical abstract

      A variety of 2-acylindoles were readily prepared from N-pyrimidyl-substituted indoles in moderate to good yields by an effective palladium-catalyzed C2-acylation method. The remarkable features of this methodology include good product yields and wide tolerance of various functional groups.

    4. Cycloaddition Reactions

      [3+2] Route to Quaternary Oxaprolinol Derivatives as Masked Precursors of Disubstituted β33-Amino Aldehyde

      Pavlo Shpak-Kraievskyi, Amelle Mankou Makaya, Anne Beauchard, Arnaud Martel, Mathieu Y. Laurent and Gilles Dujardin

      Article first published online: 6 MAY 2015 | DOI: 10.1002/ejoc.201500339

      Thumbnail image of graphical abstract

      Isoxazolidines displaying a quaternary stereocenter were formed starting from functional cyclic ketonitrones through a highly stereocontrolled 1,3-dipolar cycloaddition. Chemoselective reductive chiral auxiliary removal gives quaternary oxaprolinol derivatives, which were further transformed into dipeptides terminated directly with an aldehyde function.

    5. Helicenes

      Sterically Congested Chiral 7,8-Dioxa[6]helicene and Its Dihydro Analogues: Synthesis, Regioselective Functionalization, and Unexpected Domino Prins Reaction

      Mohammed Hasan, Anita D. Pandey, Vaibhav N. Khose, Nitin A. Mirgane and Anil V. Karnik

      Article first published online: 6 MAY 2015 | DOI: 10.1002/ejoc.201500327

      Thumbnail image of graphical abstract

      Helical dioxa[6]helicene-based systems are developed by regioselective functionalization at the sterically most hindered C1 position. An unexpected domino Prins reaction on the central double bond of the helicene skeleton is observed as a result of the strain present in the helicene backbone. The steric factors responsible for the reaction outcome are discussed.

    6. Super-Nucleophiles

      Morita–Baylis–Hillman Reactions with Nitroalkenes: A Case Study

      Vincent Barbier, François Couty and Olivier R. P. David

      Article first published online: 6 MAY 2015 | DOI: 10.1002/ejoc.201500207

      Thumbnail image of graphical abstract

      Super-nucleophilic pyridine catalysts were used to probe elementary steps of a particular reaction. As a consequence Morita–Baylis–Hillman reactions that employ nitroalkenes can now be performed with great efficiency through catalysis with remarkably low amounts of super-DMAP.

    7. Heterocyclic Chemistry

      Preparation of Halogen-Containing 4H-Pyrido[e][1,3]oxazin-4-ones and Their Transformation into 2-Hydroxypyridinyl-Substituted 1,2,4-Oxadiazoles and 1,2,4-Triazoles

      Laetitia Le Falher, Omar Ben Ayad, Ozge Ziyaret, Candice Botuha, Serge Thorimbert and Franck Slowinski

      Article first published online: 6 MAY 2015 | DOI: 10.1002/ejoc.201500277

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      Halogen-containing 4H-pyrido[e][1,3]oxazin-4-ones were synthesised by intramolecular O-arylation of the corresponding imide sodium salt precursors. The intramolecular O-arylation was studied on compounds with different halophenyl substituents. A one-step transformation of some of these pyrido-oxazinones into hydroxypyridyl-substituted 1,2,4-oxadiazoles and 1,2,4-triazoles was explored.

    8. Synthesis of 1,4-Disubstituted Pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyridazines by Means of SNAr and Palladium-Catalysed Reactions

      Rabia Belaroussi, Ahmed El Hakmaoui, Nathalie Percina, Agnes Chartier, Mathieu Marchivie, Stéphane Massip, Christian Jarry, Mohamed Akssira, Gérald Guillaumet and Sylvain Routier

      Article first published online: 6 MAY 2015 | DOI: 10.1002/ejoc.201500294

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      An efficient and convenient method for the formation of 1,4-disubstituted pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyridazines was developed. SNAr and palladium catalysed reactions gave access to the final derivatives in good to excellent yields. Each step was fully optimised.

    9. Natural Products

      The Thia-Michael Reactivity of Zerumbone and Related Cross-Conjugated Dienones: Disentangling Stoichiometry, Regiochemistry, and Addition Mode with an NMR-Spectroscopy-Based Cysteamine Assay

      Giovanni Appendino, Alberto Minassi, Juan A. Collado, Federica Pollastro, Giuseppina Chianese, Orazio Taglialatela-Scafati, Mehdi Ayyari, Victor Garcia and Eduardo Muñoz

      Article first published online: 6 MAY 2015 | DOI: 10.1002/ejoc.201500237

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      Using the NMR-spectroscopy-based cysteamine assay, the thia-Michael reactivity of the cross-conjugated dienone zerumbone and its photoisomers and epoxides was investigated, and marked differences were found. For biological endpoints sensitive to Michael acceptors, a substantial separation between reactivity and biological activity was observed.

    10. Nitrogen Heterocycles

      Efficient Access to 2,6,8-Trisubstituted 4-Aminoquinazolines through Microwave-Assisted One-Pot Chemoselective Tris-Suzuki–Miyaura or SNAr/Bis-Suzuki–Miyaura Reactions in Water

      Youssef Kabri, Maxime D. Crozet, Thierry Terme and Patrice Vanelle

      Article first published online: 5 MAY 2015 | DOI: 10.1002/ejoc.201500162

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      A sequential, one-pot strategy for synthesizing polyfunctionalized quinazoline derivatives in good to excellent yields in only a few steps and in the environmentally benign solvent water is presented. The approach uses a chemoselective Suzuki–Miyaura reaction.

    11. Suzuki–Miyaura Cross-Coupling

      Synthesis of Magnaldehydes B and E and Dictyobiphenyl B by Microwave-Promoted Cross-Coupling of Boronophenols

      Bernd Schmidt and Martin Riemer

      Article first published online: 5 MAY 2015 | DOI: 10.1002/ejoc.201500350

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      A protecting-group-free Suzuki–Miyaura cross-coupling reaction of halophenols and boronophenols by using Pd/C as the catalyst and water as the solvent under microwave irradiation has been used for the synthesis of five biphenol-type natural products.

    12. Fluorination

      Apparent Electrophilic Fluorination of 1,3-Dicarbonyl Compounds Using Nucleophilic Fluoride Mediated by PhI(OAc)2

      Toby J. Nash and Graham Pattison

      Article first published online: 5 MAY 2015 | DOI: 10.1002/ejoc.201500370

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      The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF mediated by the in-situ formation of PhIF2 from PhI(OAc)2 is reported. This can be performed safely in standard laboratory glassware, and this approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine.

    13. Indole Synthesis

      Synthesis of Chiral (Indol-2-yl)methanamines and Insight into the Stereochemistry Protecting Effects of the 9-Phenyl-9-fluorenyl Protecting Group

      Christopher S. Lood, Aino E. Laine, Antonia Högnäsbacka, Martin Nieger and Ari M. P. Koskinen

      Article first published online: 1 MAY 2015 | DOI: 10.1002/ejoc.201500391

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      Herein is presented a highly efficient stereospecific synthesis of (indol-2-yl)methanamines from amino acids together with a mechanistic study on the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group with the aid of DFT calculations, NMR and X-ray crystallography.

  24. Short Communications

    1. Chiral Industrial Azo Dye

      Simple Azo Dyes Provide Access to Versatile Chiroptical Switches

      Emmanuel Anger and Stephen P. Fletcher

      Article first published online: 1 MAY 2015 | DOI: 10.1002/ejoc.201500485

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      The azo-core of dyes can undergo trans to cis photoisomerization, which allows azobenzene derivatives to act as light triggered molecular switches. Simple derivatization of Sudan I using a chiral auxiliary provides access to chiroptical molecular switches. The properties of these switches can be readily tuned by modification of the molecular structure.

  25. Full Papers

    1. Trifunctional Scaffolds

      The Development of a Versatile Trifunctional Scaffold for Biological Applications

      Václav Vaněk, Jan Pícha, Benjamin Fabre, Miloš Buděšínský, Martin Lepšík and Jiří Jiráček

      Article first published online: 30 APR 2015 | DOI: 10.1002/ejoc.201500255

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      The development of a trifunctional scaffold derivatized with three orthogonally protected alkyne moieties that is useful for the solid-phase synthesis of combinatorial libraries is described.

    2. Dye-Sensitized Solar Cells

      Development of D–π–A Fluorescent Dyes with a 3-Pyridyl Group as Electron-Withdrawing Anchoring Group for Dye-Sensitized Solar Cells

      Yousuke Ooyama, Koji Uenaka and Joji Ohshita

      Article first published online: 30 APR 2015 | DOI: 10.1002/ejoc.201500341

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      D–π–A and (D–π–)2A fluorescent dyes with a 3-pyridyl group as an electron-withdrawing anchoring group have been newly developed, and their optical and electrochemical properties were investigated, along with their photovoltaic performance in dye-sensitized solar cells.

    3. Fluorinated Arenes

      Copper-Mediated Synthesis of Aryldifluoromethylphosphonates: A Sandmeyer Approach

      Alexandre Bayle, Chloé Cocaud, Cyril Nicolas, Olivier R. Martin, Thomas Poisson and Xavier Pannecoucke

      Article first published online: 30 APR 2015 | DOI: 10.1002/ejoc.201500373

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      The valuable diethyl phosphonodifluoromethyl moiety was introduced into arenes by employing a Sandmeyer approach. This methodology represents a convenient alternative to the need for harsh reaction conditions or expensive starting materials.

    4. C–H Activation

      Pd(OAc)2/AgOAc Catalytic System Based Bidentate Ligand Directed Regiocontrolled C–H Arylation and Alkylation of the C-3 Position of Thiophene- and Furan-2-carb­oxamides

      Rayavarapu Padmavathi, Rathinam Sankar, Bojan Gopalakrishnan, Ramarao Parella and Srinivasarao Arulananda Babu

      Article first published online: 30 APR 2015 | DOI: 10.1002/ejoc.201500249

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      A contemporary method is reported for the Pd(OAc)2/AgOAc catalytic system based bidentate ligand directed, regioselective C–H activation and C–C bond formation of the C-3 position of thiophene- and furan-2-carboxamides. This protocol was used for the direct C-3 arylation and alkylation reactions of both thiophene- and furan-2-carboxamides.

    5. Porphyrinoid Aromaticity

      Porphyrinoid Aromaticity Induced by the Interaction between Oxidized and Reduced Pyridine Subunits

      Saburo Neya, Masaaki Suzuki, Tomomi Mochizuki, Tyuji Hoshino and Akira T. Kawaguchi

      Article first published online: 29 APR 2015 | DOI: 10.1002/ejoc.201500260

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      Coupling of 3-hydroxypyridine-2,6-dicarbaldehyde with a tripyrrane-like precursor bearing a central pyridine ring afforded a new porphyrinoid with two pyridine-related subunits Spectroscopic and theoretical analyses demonstrate that the aromaticity of this porphyrinoid is fulfilled by the cooperative interaction between the two pyridinoid rings.

    6. Artemisinin Model Systems

      Model Studies on Peroxidic Glutathione Transferase (GST) Inhibitors: C5-Methylated 1,2,4-Trioxanes with C6-Acrylate Side Chains

      Axel G. Griesbeck, Andreas Maaßen, Maria Bräutigam and Markus Pietsch

      Article first published online: 29 APR 2015 | DOI: 10.1002/ejoc.201500326

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      A route to 5-methylated 1,2,4-trioxane acrylates is described. These compounds show moderate inhibition of glutathione transferase (GST).

    7. Organofluorine Compounds

      Synthesis of γ-Difluoromethyl α,β-Un­saturated γ-Butyrolactones Using PhSCF2SiMe3 as a Difluoromethylating Agent

      Arisara Issaree, Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul and Manat Pohmakotr

      Article first published online: 29 APR 2015 | DOI: 10.1002/ejoc.201500342

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      A general synthesis of γ-difluoromethyl α,β-unsaturated γ-butyrolactones is described. The method involves the fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to a masked maleic anhydride followed by reductive cleavage of the phenylsulfanyl group, reaction with Grignard reagents or NaBH4 and flash-vacuum pyrolysis.

    8. Amino Acid Protecting Groups

      Mild Oxidative Cleavage of 9-BBN-Protected Amino Acid Derivatives

      Tobias Ankner, Thomas Norberg and Jan Kihlberg

      Article first published online: 29 APR 2015 | DOI: 10.1002/ejoc.201500361

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      A representative set of 9-BBN-protected amino acid derivatives were efficiently deprotected using peracid reagents in excellent yields. Deprotection is orthogonal with several common protecting groups. Its tolerance of highly acid sensitive groups, such as trityl-protected amides and glycosidic linkages, is especially notable.

    9. Natural Products

      A Total Synthesis of Galanthamine Involving De Novo Construction of the Aromatic C-Ring

      Jeremy Nugent, Eliška Matoušová and Martin G. Banwell

      Article first published online: 29 APR 2015 | DOI: 10.1002/ejoc.201500365

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      The first synthesis of the alkaloid galanthamine is reported in which the aromatic C-ring is assembled from non-aromatic precursors. This was accomplished by a Diels–Alder cycloaddition reaction. The diene used embodies the AB-ring system (and associated quaternary carbon centre) and was constructed by intramolecular Alder-ene and Tsuji–Trost-type chemistries. The D-ring was closed by a modified Bischler–Napieralski reaction.

  26. Short Communications

    1. Chlorophyll-Derived Photosensitizers

      Chlorin e6 131:152-Anhydride: A Key Intermediate in Conjugation Reactions of Chlorin e6

      Hui Chen, R. G. Waruna Jinadasa, Lijuan Jiao, Frank R. Fronczek, Alex L. Nguyen and Kevin M. Smith

      Article first published online: 29 APR 2015 | DOI: 10.1002/ejoc.201500478

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      Standard stoichiometric peptide-type conjugations of chlorin e6 with eight oxygen and nitrogen nucleophiles proceed via the title 152,131-anhydride to give the corresponding 152-conjugate. The intermediate anhydride is definitively identified and an X-ray structure of it is reported.

  27. Full Papers

    1. Porphycenes

      You have full text access to this OnlineOpen article
      Crossed McMurry Coupling Reactions for Porphycenic Macrocycles: Non-Statistical Selectivity and Rationalisation

      Thomas Y. Cowie, Lorna Kennedy, Justyna M. Żurek, Martin J. Paterson and Magnus W. P. Bebbington

      Article first published online: 29 APR 2015 | DOI: 10.1002/ejoc.201500221

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      In the first study of its type, experimental and computational studies on crossed McMurry reactions for the synthesis of porphycenoid macrocycles reveal a marked dependence of the product profile upon the reducibility of the dicarbonyl precursors.

  28. Short Communications

    1. Pt(II)-Functionalized Crownophanes

      A Dinuclear (bpy)PtII-Decorated Crownophane

      Ilona Stengel, Günther Götz, Matthias Weil and Peter Bäuerle

      Article first published online: 14 APR 2015 | DOI: 10.1002/ejoc.201500213

      Thumbnail image of graphical abstract

      A [13.3.3](1,2,4)crownophane was designed and synthesized as a functional bridging ligand for a dinuclear PtII complex. The structure and the breathing function of the crownophane moiety were investigated in detail. Furthermore, the photophysics of the final dinuclear PtII compound were studied.

  29. Full Papers

    1. Cross-Coupling

      RhI-Catalyzed Site-Selective Decarbonylative Alkenylation and Arylation of Quinolones under Chelation Assistance

      Soonhyung Kwon, Dahye Kang and Sungwoo Hong

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500187

      Thumbnail image of graphical abstract

      The C-2 selective alkenylation and arylation reactions of 4-quinolones were achieved by using a RhI-catalyzed decarbonylative coupling strategy to afford valuable C-2 functionalized 4-quinolones. The present method was compatible with a broad scope of substrates and applied to the C-3 selective functionalization of an isoquinolone scaffold.

  30. Microreviews

    1. C–H Activation

      Ubiquitous Benzoquinones, Multitalented Compounds for Palladium-Catalyzed Oxidative Reactions

      Alexandre Vasseur, Jacques Muzart and Jean Le Bras

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500080

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      This review highlights the multifaceted properties of benzoquinone when it is involved in PdII-catalyzed oxidative reactions and presents mechanisms proposed in the literature.

    2. Azolylpurine Derivatives

      Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives

      Irina Novosjolova, Ērika Bizdēna and Māris Turks

      Article first published online: 23 MAR 2015 | DOI: 10.1002/ejoc.201403527

      Thumbnail image of graphical abstract

      This microreview describes different approaches for the synthesis of C(2)-, C(6)-, C(8)-, N(7)-, and N(9)-azolyl-substituted purine and purine nucleoside derivatives. Different methodologies including SNAr, cyclization, and transition-metal-catalyzed cross-coupling reactions are reviewed. These derivatives are important due to their wide applications in medicinal and biological chemistry.

    3. Anion Receptors

      Recent Advancements in Calix[4]pyrrole-Based Anion-Receptor Chemistry

      Indrajit Saha, Jeong Tae Lee and Chang-Hee Lee

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejoc.201403701

      Thumbnail image of graphical abstract

      Synthetic developments and anion-binding properties of newly developed calix[4]pyrroles are extensively discussed and accomplishments to date are summarized. Specifically, the formation of supramolecular organic frameworks and the possibility of customizing nanoscale structures through noncovalent interactions such as hydrogen bonding, anion–π interactions, and Coulombic interaction are addressed.

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